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NEW YORK—The sharpest thorn in the U.S. administration’s side, when it comes to civil rights in a post-9/11 world, is a mild-mannered 41-year-old Canadian who gave up Wall Street a decade ago to slip down a legal rabbit hole.

Jameel Jaffer, a Kingston, Ont., native and Upper Canada College graduate, is the head of the American Civil Liberties Union’s Center for Democracy, and in the past 10 years, he has emerged as one of the most prominent critics of secretive national security policies in the United States.

Jaffer said he had “naively” believed his work would slow under the Obama administration.

“If you had proposed 12 or 13 years ago that the United States was going to be under a Democratic president and the first African-American president, and the United States would have indefinite detention at Guantanamo, would have a statute authorizing warrantless wiretapping . . . have a targeted killing program under which the government was killing people, including American citizens, in half a dozen countries around the world without any process, you would have been thought crazy,” he said in an interview last week.

“Now it’s the new normal. If you propose we should depart from those policies, you’re thought of as a marginal voice.”

Like many ACLU battles, the drone program challenge is largely about getting information — which, as a U.S. District Court judge recently agreed, can be a surreal quest.

Earlier this month, Judge Colleen McMahon denied a request by the ACLU and the New York Times that the Justice Department disclose its legal justification for the targeted killing of an American, saying “a thicket of laws and precedents” prevented her from doing so. “The Alice-in-Wonderland nature of this pronouncement is not lost on me,” she wrote in the Jan. 2 decision, decrying the “veritable Catch-22” scenario she found herself in.

The suit concerned American Anwar al Awlaki, who was killed in a 2011 drone attack in Yemen. The ACLU and the Times had argued that the government had waived its right to keep secret the drone program’s legal rationale because administration officials had defended the attacks in public.

While acknowledging that government officials had been involved in “an extensive public relations campaign,” McMahon said the comments didn’t go far enough to overcome freedom-of-information laws protecting classified material.

Jaffer said the ACLU would appeal the case — perhaps eventually taking him once again to the Supreme Court.

His first argument there came this fall, when he challenged the government’s warrantless wiretapping of American residents and citizens, known as the Foreign Intelligence Surveillance Act, or FISA.

Critics say it won’t be an easy case to win, but tackling tough cases is how Jaffer built his reputation south of the border. In 2004, an ACLU Freedom of Information challenge forced the Bush administration to disclose details about its interrogation program.

“The litigation propelled Jameel Jaffer from an unknown and inexperienced lawyer to a hero of progressive litigation, a man at the vanguard of the national security bar who used the courts . . . to extract the government’s darkest national security secrets,” Harvard law professor Jack Goldsmith, who was an assistant attorney general in the Office of Legal Counsel under the Bush administration, wrote in his book Power and Constraint.

Even those who don’t always support Jaffer’s legal positions praise his tenacity and persuasiveness in the courts.

“The truth is, we disagree about a lot, we agree about a lot, but the guy is an unbelievably good lawyer,” said Sam Rascoff, a former director of intelligence analysis at the New York Police Department and now an associate professor of law at New York University.

Rascoff said he took his NYU students to watch Jaffer argue the FISA case before court. “I’ve heard the best lawyers in the country make arguments about every kind of issue you can imagine and I’m going to say his was the best oral argument I’ve ever heard a lawyer make,” Rascoff said.

“He’s under control, he knows his case intimately; he knows how far he can go.”

Jaffer, who hails from a line of Ismaili Muslims, was raised in Kingston by his pharmacist father and librarian mother. His parents had left Tanzania — where his mom had a brief stint as a disc jockey — for the U.K., and in 1969 settled in Canada, where Jaffer and his younger brother were born.

At 16, Jaffer attended boarding school at Upper Canada College, where math teacher Roger Allen said he quickly adapted.

“He had a charm, a sense of humour, a slight cheekiness about him that bespeaks intellect,” Allen recalled. “He’s capable of reading situations extremely well.”

After UCC, Jaffer attended Williams College, then Harvard’s law school, before putting his math degree to use at an equity derivative practice on Wall Street following the 9/11 attacks. He became involved in civil rights litigation after listening to a speech about the ACLU’s attempt to get information on those detained in widespread immigration sweeps.

“The government kept saying they were being detained in connection with the 9/11 investigation, which made it sound like these were the people who had planned the 9/11 attacks,” Jameel said.

“But after a point, when the government said we now have 1,200 people in custody, it became clear they were using that phrase pretty loosely.

“It was an important experience for me. Seeing those people in the detention facilities and seeing how desperate they were . . . We were their only link to the outside world.”

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